ZA200101507B - Method for producing ortho-alkylated benzoic acid derivatives. - Google Patents
Method for producing ortho-alkylated benzoic acid derivatives. Download PDFInfo
- Publication number
- ZA200101507B ZA200101507B ZA200101507A ZA200101507A ZA200101507B ZA 200101507 B ZA200101507 B ZA 200101507B ZA 200101507 A ZA200101507 A ZA 200101507A ZA 200101507 A ZA200101507 A ZA 200101507A ZA 200101507 B ZA200101507 B ZA 200101507B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- methylsulfonyl
- acid
- chloro
- stage
- Prior art date
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- 150000001558 benzoic acid derivatives Chemical class 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 42
- XXFKOBGFMUIWDH-UHFFFAOYSA-N 4-chloro-2-methylbenzoic acid Chemical compound CC1=CC(Cl)=CC=C1C(O)=O XXFKOBGFMUIWDH-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 150000002900 organolithium compounds Chemical group 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- YGYZEHXIHONBML-UHFFFAOYSA-N 4-chloro-2-methyl-5-methylsulfonylbenzoic acid Chemical compound CC1=CC(Cl)=C(S(C)(=O)=O)C=C1C(O)=O YGYZEHXIHONBML-UHFFFAOYSA-N 0.000 claims description 17
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 17
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
- RTIPTGMVQIIMKL-UHFFFAOYSA-N 1-bromo-4-chloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Br RTIPTGMVQIIMKL-UHFFFAOYSA-N 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001499 aryl bromides Chemical class 0.000 claims description 10
- GROMEQPXDKRRIE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GROMEQPXDKRRIE-UHFFFAOYSA-N 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 9
- UADMBZFZZOBWBB-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(N2C=CC=C2)=C1S(C)(=O)=O UADMBZFZZOBWBB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 8
- OBYSQDHKQUWQEW-UHFFFAOYSA-N 2-methyl-4,5-bis(methylsulfonyl)benzoic acid Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(O)=O OBYSQDHKQUWQEW-UHFFFAOYSA-N 0.000 claims description 8
- WCBNPNGDKPWXSF-UHFFFAOYSA-N 4-(benzylamino)-2-methyl-5-methylsulfonylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(NCC=2C=CC=CC=2)=C1S(C)(=O)=O WCBNPNGDKPWXSF-UHFFFAOYSA-N 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 235000010265 sodium sulphite Nutrition 0.000 claims description 8
- KBPZKRMZEPBEBY-UHFFFAOYSA-N 2-methyl-4,5-bis(methylsulfonyl)benzoyl chloride Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(Cl)=O KBPZKRMZEPBEBY-UHFFFAOYSA-N 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 4
- YSQFBLFEYNOIBW-UHFFFAOYSA-N lithium;cyclopropane Chemical compound [Li+].C1C[CH-]1 YSQFBLFEYNOIBW-UHFFFAOYSA-N 0.000 claims description 4
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- KLPYAEJECLFJHX-UHFFFAOYSA-N methyl 2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(C)(=O)=O)=C1N1C=CC=C1 KLPYAEJECLFJHX-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229960001922 sodium perborate Drugs 0.000 description 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GVPDEGIDDNGBTL-UHFFFAOYSA-N 2-methyl-4-methylsulfanyl-5-methylsulfonylbenzoic acid Chemical compound CSC1=CC(C)=C(C(O)=O)C=C1S(C)(=O)=O GVPDEGIDDNGBTL-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- ZDZPGBYACWZEJJ-UHFFFAOYSA-N 4-amino-2-methyl-5-methylsulfonylbenzoic acid Chemical compound CC1=CC(N)=C(S(C)(=O)=O)C=C1C(O)=O ZDZPGBYACWZEJJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001503 aryl iodides Chemical class 0.000 description 2
- 230000021523 carboxylation Effects 0.000 description 2
- 238000006473 carboxylation reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000006138 lithiation reaction Methods 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CENDNMZQRHKPMC-UHFFFAOYSA-N methyl 4-(benzylamino)-2-methyl-5-methylsulfonylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(C)(=O)=O)=C1NCC1=CC=CC=C1 CENDNMZQRHKPMC-UHFFFAOYSA-N 0.000 description 2
- QBVGRWIWDJZYAP-UHFFFAOYSA-N methyl 4-amino-2-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(N)C=C1C QBVGRWIWDJZYAP-UHFFFAOYSA-N 0.000 description 2
- -1 methyl tert-butyl Chemical group 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ORKKSDGNUXWYKI-UHFFFAOYSA-N 2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(N2C=CC=C2)=C1S(C)(=O)=O ORKKSDGNUXWYKI-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 102000003669 Antiporters Human genes 0.000 description 1
- 108090000084 Antiporters Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- INGSNHMAAYVQPH-UHFFFAOYSA-N methyl 4-chloro-2-methyl-5-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(Cl)C=C1C INGSNHMAAYVQPH-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SUZXWXGJCOCMHU-UHFFFAOYSA-N n-sulfonylbenzamide Chemical compound O=S(=O)=NC(=O)C1=CC=CC=C1 SUZXWXGJCOCMHU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010641 nitrile hydrolysis reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007122 ortho-metalation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B18/00—Use of agglomerated or waste materials or refuse as fillers for mortars, concrete or artificial stone; Treatment of agglomerated or waste materials or refuse, specially adapted to enhance their filling properties in mortars, concrete or artificial stone
- C04B18/02—Agglomerated materials, e.g. artificial aggregates
- C04B18/021—Agglomerated materials, e.g. artificial aggregates agglomerated by a mineral binder, e.g. cement
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00767—Uses not provided for elsewhere in C04B2111/00 for waste stabilisation purposes
- C04B2111/00775—Uses not provided for elsewhere in C04B2111/00 for waste stabilisation purposes the composition being used as waste barriers or the like, e.g. compositions used for waste disposal purposes only, but not containing the waste itself
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/91—Use of waste materials as fillers for mortars or concrete
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998133118 DE19833118C2 (de) | 1998-07-23 | 1998-07-23 | Verfahren zur Herstellung von orthoalkylierten Benzoesäurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200101507B true ZA200101507B (en) | 2002-05-22 |
Family
ID=7875019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200101507A ZA200101507B (en) | 1998-07-23 | 2001-02-22 | Method for producing ortho-alkylated benzoic acid derivatives. |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6350904B1 (hu) |
| EP (1) | EP1098866B1 (hu) |
| JP (1) | JP2002521352A (hu) |
| KR (1) | KR20010053294A (hu) |
| CN (1) | CN1190406C (hu) |
| AR (1) | AR020620A1 (hu) |
| AT (1) | ATE259343T1 (hu) |
| AU (1) | AU756673B2 (hu) |
| BR (1) | BR9912319A (hu) |
| CA (1) | CA2338300A1 (hu) |
| DE (2) | DE19833118C2 (hu) |
| DK (1) | DK1098866T3 (hu) |
| ES (1) | ES2216540T3 (hu) |
| HK (1) | HK1039478A1 (hu) |
| HU (1) | HUP0102657A3 (hu) |
| ID (1) | ID27856A (hu) |
| NO (1) | NO20010365D0 (hu) |
| PL (1) | PL345284A1 (hu) |
| PT (1) | PT1098866E (hu) |
| SK (1) | SK852001A3 (hu) |
| TW (1) | TW546285B (hu) |
| WO (1) | WO2000005187A1 (hu) |
| ZA (1) | ZA200101507B (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003028183A1 (en) | 2001-09-28 | 2003-04-03 | Commvault Systems, Inc. | System and method for generating and managing quick recovery volumes |
| AU2003279847A1 (en) | 2002-10-07 | 2004-05-04 | Commvault Systems, Inc. | System and method for managing stored data |
| WO2005050385A2 (en) | 2003-11-13 | 2005-06-02 | Commvault Systems, Inc. | System and method for performing integrated storage operations |
| US8959299B2 (en) * | 2004-11-15 | 2015-02-17 | Commvault Systems, Inc. | Using a snapshot as a data source |
| DE102005005946A1 (de) * | 2005-02-10 | 2006-08-17 | Basf Ag | Verfahren zur Herstellung tertiärer Phosphine |
| US7928591B2 (en) * | 2005-02-11 | 2011-04-19 | Wintec Industries, Inc. | Apparatus and method for predetermined component placement to a target platform |
| JP4641839B2 (ja) * | 2005-03-23 | 2011-03-02 | セントラル硝子株式会社 | ４−メチル−３−トリフルオロメチル安息香酸の製造方法 |
| US20100312013A1 (en) * | 2009-06-03 | 2010-12-09 | Boehringer Ingelheim International Gmbh | Steroselective synthesis of certain trifluoromethyl-substituted alcohols |
| US9092500B2 (en) | 2009-09-03 | 2015-07-28 | Commvault Systems, Inc. | Utilizing snapshots for access to databases and other applications |
| US8719767B2 (en) | 2011-03-31 | 2014-05-06 | Commvault Systems, Inc. | Utilizing snapshots to provide builds to developer computing devices |
| CA2783370C (en) * | 2009-12-31 | 2016-03-15 | Commvault Systems, Inc. | Systems and methods for performing data management operations using snapshots |
| WO2011082132A1 (en) | 2009-12-31 | 2011-07-07 | Commvault Systems, Inc. | Systems and methods for analyzing snapshots |
| AU2012262489A1 (en) * | 2011-05-27 | 2013-04-04 | Icahn School Of Medicine At Mount Sinai | Substituted 2-benzylidene-2H-benzo[b][1,4]thiazin-3(4H)-ones, derivatives thereof, and therapeutic uses thereof |
| CN106365978B (zh) * | 2016-08-31 | 2019-01-11 | 绍兴上虞华伦化工有限公司 | 一种2,3-二氟-6-甲氧基苯甲酸的制备方法 |
| CN115448831B (zh) * | 2022-11-10 | 2023-02-03 | 北京元延医药科技股份有限公司 | 制备4-乙酰基-1-萘甲酸的方法 |
| CN116425623B (zh) * | 2023-04-10 | 2024-02-13 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8613207D0 (en) * | 1986-05-30 | 1986-07-02 | Yarsley Technical Centre Ltd | Trifluoromethyl aromatic compounds |
| DE59305042D1 (de) * | 1992-09-22 | 1997-02-20 | Hoechst Ag | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
| DE4430213A1 (de) * | 1994-08-28 | 1996-02-29 | Merck Patent Gmbh | Arylbenzoylguanidine |
| DE4430861A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Heterocyclyl-benzoylguanidine |
| DE19529612A1 (de) | 1995-08-11 | 1997-02-13 | Merck Patent Gmbh | Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate |
-
1998
- 1998-07-23 DE DE1998133118 patent/DE19833118C2/de not_active Expired - Fee Related
-
1999
- 1999-07-06 DK DK99934577T patent/DK1098866T3/da active
- 1999-07-06 ID ID20010281A patent/ID27856A/id unknown
- 1999-07-06 SK SK85-2001A patent/SK852001A3/sk unknown
- 1999-07-06 JP JP2000561144A patent/JP2002521352A/ja active Pending
- 1999-07-06 DE DE59908523T patent/DE59908523D1/de not_active Expired - Fee Related
- 1999-07-06 PT PT99934577T patent/PT1098866E/pt unknown
- 1999-07-06 EP EP19990934577 patent/EP1098866B1/de not_active Expired - Lifetime
- 1999-07-06 CN CNB998090085A patent/CN1190406C/zh not_active Expired - Fee Related
- 1999-07-06 ES ES99934577T patent/ES2216540T3/es not_active Expired - Lifetime
- 1999-07-06 US US09/744,302 patent/US6350904B1/en not_active Expired - Fee Related
- 1999-07-06 HU HU0102657A patent/HUP0102657A3/hu unknown
- 1999-07-06 CA CA 2338300 patent/CA2338300A1/en not_active Abandoned
- 1999-07-06 PL PL34528499A patent/PL345284A1/xx unknown
- 1999-07-06 BR BR9912319A patent/BR9912319A/pt not_active IP Right Cessation
- 1999-07-06 KR KR1020007015017A patent/KR20010053294A/ko not_active Application Discontinuation
- 1999-07-06 AU AU50314/99A patent/AU756673B2/en not_active Ceased
- 1999-07-06 WO PCT/EP1999/004674 patent/WO2000005187A1/de not_active Application Discontinuation
- 1999-07-06 AT AT99934577T patent/ATE259343T1/de not_active IP Right Cessation
- 1999-07-21 TW TW88112363A patent/TW546285B/zh active
- 1999-07-23 AR ARP990103626 patent/AR020620A1/es not_active Application Discontinuation
-
2001
- 2001-01-22 NO NO20010365A patent/NO20010365D0/no unknown
- 2001-02-22 ZA ZA200101507A patent/ZA200101507B/en unknown
-
2002
- 2002-01-08 US US10/038,602 patent/US6515143B2/en not_active Expired - Fee Related
- 2002-02-08 HK HK02101006.8A patent/HK1039478A1/zh unknown
- 2002-10-08 US US10/265,607 patent/US6573404B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO20010365L (no) | 2001-01-22 |
| HUP0102657A2 (hu) | 2001-11-28 |
| DE19833118A1 (de) | 2000-02-03 |
| JP2002521352A (ja) | 2002-07-16 |
| US20020091286A1 (en) | 2002-07-11 |
| WO2000005187A1 (de) | 2000-02-03 |
| PL345284A1 (en) | 2001-12-03 |
| EP1098866A1 (de) | 2001-05-16 |
| US6573404B2 (en) | 2003-06-03 |
| SK852001A3 (en) | 2001-08-06 |
| KR20010053294A (ko) | 2001-06-25 |
| ATE259343T1 (de) | 2004-02-15 |
| NO20010365D0 (no) | 2001-01-22 |
| DK1098866T3 (da) | 2004-06-01 |
| ID27856A (id) | 2001-04-26 |
| EP1098866B1 (de) | 2004-02-11 |
| AR020620A1 (es) | 2002-05-22 |
| CA2338300A1 (en) | 2000-02-03 |
| HUP0102657A3 (en) | 2002-03-28 |
| DE59908523D1 (de) | 2004-03-18 |
| US6515143B2 (en) | 2003-02-04 |
| CN1310700A (zh) | 2001-08-29 |
| TW546285B (en) | 2003-08-11 |
| HK1039478A1 (zh) | 2002-04-26 |
| BR9912319A (pt) | 2001-05-08 |
| AU756673B2 (en) | 2003-01-23 |
| AU5031499A (en) | 2000-02-14 |
| CN1190406C (zh) | 2005-02-23 |
| ES2216540T3 (es) | 2004-10-16 |
| US20030069444A1 (en) | 2003-04-10 |
| DE19833118C2 (de) | 2000-07-27 |
| PT1098866E (pt) | 2004-06-30 |
| US6350904B1 (en) | 2002-02-26 |
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